Crease proofing of cellulosic textile materials



United States Patent" '0 3,023,129 CREASE PROOFING F CELLULOSIC TEXTILE MATERIALS Solomon P. Hersh, South Charleston, W. Va., and Cal Y. Meyers, Princeton, NJ., assignors to Union Carbide Corporation, a corporation of New Yorlr No Drawing. Filed Nov. 8, 1957, Ser. No. 695,222

9 Claims. (Cl. 117-1394) rial.

It has long been known that cellulosic fibers and textile materials such as cottons and rayons exhibit a number of undesirable properties from the standpoint of wearing ability, washability, and appearance. Specifically, cotton and rayon fabrics and textile materials wrinkle and crush easily after wearing and present an undesirable mussed appearance in a short time. Similarly, fabrics made from these materials are badly wrinkled after washing and require ironing before they achieve a satisfactory appearance. Many of these fabrics, particularly those made from rayon lack good dimensional stability and will shrink considerably upon washing. It has, therefore, been found to be highly desirable to impart wrinkle and muss resistance to these fabrics, and to secure where possible dimensional stability.

A number of chemicals and resins have been suggested as a means for increasing dimensional stability and the wrinkle and crease resistance of such fibers and fabrics in order to counteract these undesirable properties. However, only two basic types of resins have been found to be at all commercially acceptable for use with cotton and rayon fabrics. These types include the melamineformaldehyde resins and ureaor cyclic urea-formaldehyde condensates. In most cases these materials are applied to the fabric by padding from a water solution containing a curing catalyst, drying the fabric and then heating to a temperature about 300 C. to cure the resin on the fibers, and followed by washing, rinsing, and dry- However, such crease and wrinkle resisting and stabilizing treatments are in themselves not without adverse effect upon the properties of the fabric. They not only seriously degrade the mechanical strengths of the fibers, particularly the tensile and tear strength, but also impart a serious chlorine-retention problem. When exposed to hypochlorite bleaching solutions, these resins absorb chlorine which is liberated as hydrochloric acid on heating, such as occurs in ironing or pressing, to further degrade the fibers. Furthermore, the high curing temperature necessary for thermally setting these treating agents is undesirable since fabric degradation and loss of strength is encountered. In most cases such high temperatures are secured only with special equipment.

Other disadvantages result from the use of melamine and urea resins, such as color development of the resin while on the fabric, particularly upon exposure to chlorine-containing bleaches. This limits the marketability of the treated material and makes their use undesirable for many applications. Previous attempts to apply phe- 3,023,129 Patented Feb. 27, 1962 nol-formaldehyde resins have similarly been frustrated by the inherent color of such condensates or by discoloration caused by light and heat. A characteristic bad odor development caused by these resins has further served to prevent the commercial development of such resins.

It is, therefore, an object of the present invention to provide a crease and wrinkle proofing method for cellulosic fibers and fabrics which will not seriously atfect the mechanical properties 991 appearance of the fabric.

It is a further object of the present invention to provide a method for crease proofing cellulosic textiles and improving dimensional stability without incurring or imparting to the fabric discoloration created'by light and odor development caused by the resin.

It is still a further object of this invention to provide a curable thermosetting resin treatment of cellulosic materials which will impart crease resistance and dimensional stability to the treated material but will not absorb chlorine or cause degradation of mechanica properties as commonly associated with chlorine retention.

It has now been discovered that a cellulose textile material treated with a resinous condensate based on 2,4,6- trimethylolphenol will have significantly improved physical properties. In particular, it has been found that the crease and wrinkle resistance of such treated materials is greatly improved without impairment of mechanical strength caused by chlorine retention. After exposure to chlorine-containing bleaches, substantially no chlorine. is retained in the treated textile materials of this invention which could cause the degradative results occasioned by the use of heretofore known crease-proofing agents. In addition, it has also been found that there is no serious odor development occasioned to the use of such resins as was often encountered heretofore.

The condensation resins imparting these improved physical properties to cellulose textile materials contain as the main resin forming ingredient a substantial amount of 2,4,6-trimethylolphenol or itsalkali or alkaline earth metal salt, i.e., the sodium, potassium, calcium, barium, strontium, ete., salt of the 2,4,6-trimethylolpheno]. The resins are the resinous condensation product of the 2,4,6-trimethylolphenol or its metal salt with an aliphatic polyhydric compound.

The cellulose textile materials can be treated in accordance with this invention by impregnating the textile materials with a solution containing the 2,4,6-trimethylolphenol or its alkaline metal salt, and the aliphatic polyhydric compound, and curing the resin-forming materials to the water-insoluble resin.

Among the aliphatic polyhydric compounds which have been found to form particularly desirable resins for use in this invention with the 2,4,6-trimethylolphenol or its alkaline metal salt are the lower aliphatic diols and polyols, for instance ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, pentamethylene glycol, propanediols, pentanediols, hexanediols, glycerine, pentaerythritol, sorbitol, inositol, and the" like. Other aliphatic hydroxyl-containing polymeric materials such as polyoxyethylene glycol, polyvinyl alcohol, hydroxyethylated polyvinyl alcohol, and polyvinyl acetate in which a portion of the acetate groups has been hydrolyzed to hydroxyl groups can also be employed. The lower molecular weight glycols and diols such as ethylene glycol and 'LS-pentanediOl condensation products with tn"- methylolphenol are particularly preferred as the crease proofing agent for most general applications. However,

'dependi'ng'upon the stiffness or fabric hand desired for the aromatic rings of the resin by a greater distance which reflects on the flexibility ofthe resin and ultimately the'flexibility and hand of the treated fiber or fabric.

With the resins prepared from trimethylolphenol and lower-aliphatic diols and glycols, it is preferred that the trimethylolphenol or its alkaline metal salt be employed in about equimolar amounts to the polyhydroxy compounds, although if desired, greater amounts of trimethylolphenol not reacted withthe glycol or diol in the resin will self-condense and give similar results in crease and wrinkle resistance to die fabric.

For lasting permanence of crease proofing effect, and

'- particularly for substantial water insolubility of the resin,

the amount of the aliphatic polyhydroxy compound should be present in amounts of not greater than about 4 moles per mole of trimethylolpheiiol. Amounts greater than this seriously affect the water solubility of the resin and the degree of crease resistance imparted to the fabric.

The copolymeric trimethylolphenol resins employed in this invention are substantially water-soluble before curing and must be applied to the" cellulosic textile material in the uncured state in order to achieve the crease and wrinkle resistance. Without desiring to be bound by any particular theory, it is believed that the resin in its soluble form is absorbed into the cellulosic fibers and curing in situ cross-links cellulosie molecules or chains to each other and to polymeric chains of the resin. Thus, increased rigidity and springiness is imparted to the celluosic fibers to secure the desired crease and wrinkle resistance.

Relatively small amounts of these trimethylolphenol resins have been found to impart the crease and wrinkle resistance to the cellulosic textile materials. Generally amounts of about three parts or more of resin per hundred parts by weight of cellulose content of the textile material will secure sufficient crease proofing etfect for most applications during the normal service life of the textile material. Amounts of between about 5 to 15 parts by weight per hunder parts of cellulose have been found to be preferred. However, for special applications, amounts of as high as 25 parts per hundred parts of cellulose can be employed without any serious effect on the physical properties of the fabric. Amounts greater than this are undesirable, not only from a cost standpoint but also from the effect of so much resin on the fabric. Amounts greater than this impart a harsh hand to the fabric and make it somewhat stiff.

The water-solubility of these resins before curing makes their application from aqueous solution extremely convenient, although if desired, other solvents can be used. Solvents such as low boiling, low molecular weight alcohols or water-alcohol mixtures, ketones, for instance acetone, or other inert solvents, such asdioxane, can be advantageously employed. Other solvents which form emulsions with the resin-forming material can also be used. Any solvents should, of course, be sufficiently volatile as to be easily removed from the fabric or fibers without damage thereto.

However, as with most applications where either aqueous or volatile solvent methods can be employed, the aqueous method is generally preferable. Hazardous 4 ads, and inherent losses of solvent in the process are thereby avoided.

A particularly desirable feature of the use of these trimethylolphenol resins is in the ability of the resins to be prepared inand applied from the same aqueous solution. The high degree of water solubility of the 2,4,6-trimethylolphenol and its alkaline metal salts, and also of the polyhydric coreactants if employed, makes it possible to prepare the resin solution by adding the resin forming monomers to water and applying the formed solutions directly to the cellulosic fabric or fibers being treated. No further polymerization or procuring the resin in solution is necessary before applying the solution to the fabric or fibers. The resin is then cured in situ to the water insoluble state in the cellulosic material to secure the crease and wrinkle proofing effect.

Water or solvent content in the treating solution is not narrowly criticaland any suitable solution giving good distribution of resin solution on and into the cellulosic fibers or fabric can be employed. The most satisfactory concentration of resin in the solution should be determined by the amount of resin to be applied, the wetability and absorption characteristics of the fibers or fabric to the solution and the particular application method employed.

A reasonably good correlation exists in the concentration of solution to the amount of resin applied. Most all cotton and rayon fabric tend to absorb between about 50 percent to percent of their weight of the treating solution. Thus in practice there can be as little as 3 parts by weight of the resin or resin forming reactants to 100 parts by weight per 100 parts of the volatile liquid. For most applications, it is preferred that the resin containing solution constitute between about 5 to 50 parts by weight of the trimethylolphenol resin.

The method of application of the trimethylolphenol resins to the cellulosic. fibers or fabrices is not restricted. For instance, the resin in solution can be applied by conventional padding techniques, or by dipping or spraying methods, followed by squeezing the fabric or fibers between rolls to control the amount of resin-containing solution picked up and to make sure all fibers are adequately wetted with the resin solution. The resin can then be cured to the water-insoluble state on the cellulosic material by heating the treated material to the desired curing temperature, or if desired, to heat to a temperature sufficient'to dry the fabric and then advance the temperature for a time sufiicient to cure and set the resin. After this curing treatment, the resin is permanently fixed to the cellulose fibers and made substantially water-insoluble as evidenced by the fact that only very slight losses are incurred in washing the fabric, even through extended washings in home laundry machines in the presence of soaps and detergents.

The temperature of the treating bath or treating solution during the application to the fabric is not critical. While room temperature solutions are most convenient, the solution can, if desired, be at an elevated temperature up to about the boiling point of the solvent employed. It is preferred that the solvent boiling point be about 100 C. or less where heat curing methods above 100 C. are employed, and even lower boiling points when lower curing temperatures are used.

It is highly advantageous that these trimethylolphenol resins can be suitably cured at low curing temperatures. Adequate curing of these resins can in many instances be secured at room temperatures. However, for most applications, it is desired that the resins be thermally cured at elevated temperatures to hasten the curing time and decrease the in-process time of the fabrics. Very suitable results can be secured at temperatures between about 100 C. to C. At such temperatures, adequate thermal cure of the resins is achieved without need of a handling of inflammable mixture os ly recovery meth- (5 catalyst to secure substantially permanent crease and wrinkle resistance of the fabric during its normal service life. 1

Highly satisfactory curing rates are also secured by the use of acidic catalysts when even faster curing times are desired. Acidic agents capable of reducing the initial pH of resin solution below about are suitable for this purpose. Acids such as phosphoric, sulfuric, hydrochloric, oxalic, or sulfamic can be employed to effect this result, as can such acid-engendering agents as acidic salts, for instance ammonium sulfamate, or .-acidic esters as his- (beta-chloroethyl) phosphate or other suitable acid-releasing agents which are capable of reducing the pH of the mixture to 5 or less.

Phosphoric acid has been found to be the preferred catalyst in that no effect on color or tensile properties on the fibers or fabrics is occasioned by its use. Most efiective results with this curing catalyst are achieved when it it employed in amounts of from 2 to percent by weight.

The catalyst, when employed, is preferably added directly to the treating solution. No adverse efiects are incurred on the resin by this direct addition to the solution. However, if desired, other methods of applying the curing catalyst as by spraying or by vapor treatments can also be used.

We have found that this catalytic curing can be conveniently accomplished in 3 to 5 minutes at about 110 C.160 C. if the resin-wet fabric is first dried at 80 C. before curing. Equally satisfactory curing can also be accomplished in to 45 minutes at temperatures of 110 C.-140 C. without this prior drying step. Curing at temperatures below about 130 C. is highly advantageous in that no special or expensive equipment is ordinarly needed to attain such conditions. Significantly, the strengths of the fibers and fabrics are not greatly affected by these resins or by the exposure to such curing temperatures, as isthe case with urea resins and to a lesser extent with the melamine resins.

The cellulosic fabrics treated in accordance with this invention are substantially unafiected in visual appearance from the untreated materials. Inasmuch as the trimethylolphenol resins herein used are essentially crystal clear or water white, no adverse effect upon the color of fabric is imparted in the fabric treatment and curing of the resins. While there may be some slight yellowing of the resins when in contact with iron-containing salts, no serious adverse efiect upon color is evident by washing in relatively iron-free water or by subsequent ironing or pressing operations.

Particularly beneficial results in strengths of the treated fabrics are secured with the trimethylolphenol resins both after curing and after bleaching. Contrary to the experience with the presently known crease and wrinkle proofing agents which seriously degrade during the application process or because of chlorine retention, the trimethylolphenol resin treated fabrics are not damaged during curing or by retained chlorine. There is no evidence of retained chlorine after contact withchlorine-containing bleaches caused by the resin employed herein.

These features have constituted the principal disadvantages to the urea and melamine type crease and wrinkle proofing agents heretofore known. Tests have indicated that very little loss in strength is caused by the application and curing of the trimethylolphenol resins and no loss in strength results after chlorine treatment, whereas with urea and melamine type resins, the loss in tensile strength generally amounts to from 35 to 70 percent or more, due either to degradation during application or to the damage caused by retained chlorine.

Highly desirable dimensional stability of the resin is also secured with the treatment of the cellulosic textile materials with the trimethylolphenol resins according to this invention. In addition, no obnoxious odors develop from their use, nor are there odors typical of phenolic resins imparted to the treated fabrics.

As employed herein, the terms cellulosic textile -or textile material are meant to encompass not only cotton and rayon fabrics and fibers but also mixtures of either with non-cellulosic materials in which the cellulose content is at least 60 percent by weight.

The following examples are illustrative.

EXAMPLE 1 Seven hundred grams of an aqueous solution containing 150 grams total of 2,4,6-trimethylolphenol and ethylene glycol in a 1:1 molar ratio was prepared and 7.5 grams (5%) of phosphoric acid was added to the solution as a catalyst. A 4-inch by ll-inch piece of cotton percale fabric was then thoroughly impregnated with the solution and the excess solution removed by passing the fabric through squeeze rolls of a hand wringer. The fabric contained approximately 50 percent by weight of the resin solution. The fabric was then dried and the resin cured by heating for 20 minutes at C. The

fabric after curing was found to contain 12 percent by weight of resin permanently aflixed on the fabric. It was determined that this resin was chemically combined with the fabric because of the fact that the fabric lost only 0.2 percent of its weight after one wash in an automatic home laundry machine and only an additional 0.2 percent of its weight after a second wash. The original fabric and the treated fabric were then evaluated for wrinkle recovery properties by the Test Method 66-53 of the American Association of Textile Chemists and Colorists employing a Monsanto Wrinkle Recovery Tester. This test includes the folding of a fabric once and placing the fold under a 1.5 lb. load for 1% minutes. After this time, the load is removed and the sample a.l lowed to recover. The recovery angle is immediately measured, measured again after one minute, and again after five minutes. Three samples were creased in the warp direction and three samples in the filling direction. All the reported values are the average of six. values after five minutes recovery. Wrinkle recovery was measured in the same method after each of two washings in an automatic home washing machine. The improvement in wrinkle recovery realized by the use of the trimethylol phenol-ethylene glycol resin is summarized in the following table:

Table I WRINKLE RECOVERY AND EXTRACTION OF FABRIC FINISHED WITH TBIMETHYLOLPHENOL-ETHYLENE GLYCOL RESIN The tensile properties and chlorine retention properties of treated sample fabrics were evaluated as follows:

Samples of fabric were prepared in the manner above described in Example I to secure resin treated cloth having about 4 percent by weight of resin. After curing, the fabrics were washed for five minutes in a solution containing 6 grams of nonionic detergent (Tergitol NPX) per liter. Properties of the cloth were then determined. Tensile strength was determined by the ravelled strip method and tear strength was determined by the tongue method, both according to ASTM standard D-39-49. These tests were both conducted on an Instrom Machine with an extension velocity of 2 inches per minute on samples clamped 2 inches apart by means of jaws. A strip of fabric lie-inch wide is obtained and ravelled spasmsbreaking strength of the Pinch wide sample is then determined on the Instrom machine.

In the tear test, a 1% inch slit is made irrone end of a- 3"X8" piece of fabric parallel to the long dimension. One of these 1% inch wide tongues is placed in each jaw of the Instron tester and the force required to tear the fabric is then noted. In each one of these tests three samples were measured in the warp direction and three in the filling direction.

After treatment of the fabric with the resin as in Example I, resistance to chlorine damage was then determined. The resistance to damage caused by retained chlorine was determined by the Testing Method 69-52 of the American Association of Textile Chemists and Colorists. The samples were treated with a solution of sodium hydrochloride containing about 0.25 percent of available chlorine (commercial Chlorox diluted 20:1 with water). The control sample and the treated sample were both then oven dried at 60 C. and scorched with a hat iron at 185 C. for 30 seconds. The scorching process liberates hydrogen chloride from any retained chlorine. The tensile strength of three samples was measured in the filling direction by the ravelled strip method as before and compared with control samples which had been scorched only.

The results are as follows, compared with an untreated control fabric of the same kind that was not resin finished, wrinkle recovery being measured in the same way as in Example 1.

by the Rohm and Haas Co. The resin was applied according to the manufacturer's directions as follows:

One hundred twenty-five parts of resin were dissolved in water at 120 F. and 6.25 parts of an alkanolamine hydrochloride catalyst sold under the name of catalyst 6-8 by the Rohm and Haas Co. diluted about 4:1 with cold water was added. The total weight'of the bath was brought to 500 parts with cold water. The final bath temperature was about 90 F.

Experiment B was a methylated trimethylol melamine resin having a solids content of about percent and sold under the name of Aerotex M-3 by the American Cyanamid Co. The resin was applied according to the manufacturers directions as follows:

One hundred fifty-six parts of M-3 resin mix was diluted with water at 80 C. and 8.8 parts of triethanolamine hydrochloride catalyst sold under the name of Aerotex Accelerator UTX by the American Cyanamid Co. was added and the mixture brought to 1000 parts by addition of water.

Application of both solutions was the same to samples of the same cloths used in showing the effect of the treatment with resins according to this invention. The cloth was dipped into the resin solution and squeezed dry with a hand wringer and dried at 60 C. and then cured for 4 minutes at 300' F. Samples were washed for 5 minutes in a dilute nonionic detergent solution (6 grams Tergitol NPX per liter) at 120 F., were rinsed well and dried.

For purposes of comparison with known wrinkle Table II Percent resin Strength retained Chlorine Tensile Tensile on tsbrlc after application damage strength Wrinkle she 11 Fabric (percent alter recovery, of 011 ml dlflerchlorine degrees tsbrlc, Wet Cured Tensile, Tear, once in damage, lbs.

percent percent strength) lbs.

Contra percale.- 0 0 +l3 43 4040 40 Treats: groom--- 6.2 4.0 78 38 -3 75 Contra" rrlugbono. 0 0 +18 70 b0 00 Treetet: herringbone-.. 8.0 8.9 104 57 2 60 78 The following results were secured:

Table III Percent m Btrsn h retained Chlorine Tensile Tensile on labrlc nlterg ppllcatlon damage strength Wrinkle strength Fabric (percent after recovery. or original dlflerchlorine d fabric, Wet Cured Tensile. Tear, ence in damage, lbs.

percent percent strength) lbs.

Experiment A rcsls 4. 6 3. 8 66 23 --4 25 110 Experiment B grails MI 5. 3 76 32 -46 17 Control parcels 0 0 +13 43 40-50 40 Experiment A herrlngbone.- 5.6 8. 2 61 43 1 ll. Experiment B herringbonm. 7.3 8.8 79 48 33 38 85 Control buringbone" 0 0 +18 70 50 and crease proofing agents, two commercially employed 70 EXAMPLE 3 materials were also tested in the same: manner.

Experiment A was a dimethylol cyclic ethylene urea resin having a specific gravity of 1.15 and a solids content of 50 percent, sold under the name of Rhonite R-l The following results presented in tabular form represent the data obtained on a series of runs employing different cellulosic fabrics and different methods of curing the resin. The resin used and the method of application and testing were the same as described in Example 1.

WRINKLE RECOVERY AND EXTRACTION OF FABRICS TESTED WITH TMP-EG Curing conditions Resin on fabric Wrinkle recovery Dried at Fabric Time Temp. Applied Extracted First;

(min.) 0.) (percent) First wash (percent) Second wash Second (degrees) wash (degrees) wash (percent) 5586 ssasaaeasasaw mucosa NwGN 'qawa GIN:

eaasaaaasaase 'seaeasaaaesssea I Control.

EXAMPLE 4 The following results presented in tabular form represent the data obtained on a series of runs employing different resins as described heretofore. The methods of application and of testing are the same as described in Example 1.

Table V WRINKLE RECOVERY AND EXTRACTION OF FABRICS FINISHED WITH TRIMETHYLOLPHENOL ALONE AND MIXED WITH OTHER COMPOUNDS Resin on fabric Wrinkle re covery after- Mole ratio, Extracted Resin 'IMP/ Apeddiplied, First Second tive per- First Second wash wash cent wash wash (de- (de- (p r- (p ar es) s cent) cent) None 2. 4 01 01 30 30 'lrimethylolphenol. 5. 2 02 63 120 100 TM P-Ethylene GlycoL 1/1 6. 5 .66 37 120 105 3/1 5. 1 03 02 120 110 Do 1/3 4. 8 l. 2 i2 100 90 Calcium Salt of TMP-Ethylene Glycol 1, 1 5. 9 81 36 100 90 TMP-PentanedioL. 1/1 4. 3 1. 56 110 100 NorE.TMP=2,4,6-trimethylolphenol.

We claim:

1. A cellulose textile material containing a substantially water-insoluble condensation resin in amounts at least sufficient to impart improved crease and wrinkle resistance but less than that amount imparting stifiness and harsh hand to the said textile material, said condensation resin being the cured product of a watersoluble resin-forming admixture of (a) a 2,4,6-trimethylolphenol compound selected from the group consisting of 2,4,6-trimethylolphenol, the alkali metal salts of 2,4,6- trimethylolphenol and the alkaline earth metal salts of 2,4,6-trimethylolphenol, and (b) a water-soluble aliphatic polyhydric compound present in amounts of no greater than about four moles per mole of the said 2,4,6-trimethylolphenol compound.

2. A cellulose textile material as described in claim 1 wherein the textile material contains between 3 and parts by weight of the water-insoluble condensation resin per parts by dry weight of the cellulose in the said textile material.

3. A cellulose textile material as described in claim 2 wherein the aliphatic polyhydric compound is a lower aliphatic diol.

4. A cellulose textile material as described in claim 3 wherein the textile material contains between 5 and 15 parts by weight of the water-insoluble condensation resin per hundred parts by dry weight of the cellulose in the said textile material.

5. A method for improving the crease and wrinkle resistance of cellulose textile materials which comprises treating the said material with asolvent solution containing per 100 parts by weight of solvent from 3 to 100 parts by weight of a water-soluble, resin-forming admixture of (a) a 2,4,6-trimethylolphenol compound selected from the group consisting of 2,4,6-trimethylolphenol, the alkali metal salts of 2,4,6-trimethylolphenol and the alkaline earth metal salts of 2,4,6-trimethylolphenol and (b) a water-soluble aliphatic polyhydric compound present in amounts of no greater than about four moles per mole of said 2,4,6-trimethylolphenol compound until the said material contains between 3 and 25 parts by Weight of resin-forming ingredients in said admixture per 100 parts by dry weight of cellulose in the said material, but in amounts less than that amount imparting stifiness and harsh hand to the said textile material, and thereafter drying the so treated material and curing the resin-forming admixture to a substantially water-insoluble resin.

6. A method according to claim 5 in which the aliphatic polyhydric compound is a lower aliphatic diol.

7. A method according to claim 6 wherein an acidic curing agent is employed to maintain the pH of the solution to less than about 5 to hasten the curing.

8. A method for improving the crease and wrinkle resistance of cellulose textile materials which comprises treating said material with an aqueous solution containing per 100 parts water, from 3 to 100 parts by weight of a water-soluble, resin-forming admixture of (a) a 2,4,6- trimethylolphenol compound selected from the group consisting of 2,4,6-trimethylolphenol, the alkali metal salts of 2,4,6-trimethylclphenol, and the alkaline earth metal salts of 2,4,6-trimethylolphenol and (b) a water-soluble aliphatic polyhydric compound present in amounts of no 11 water than four moles per mole of said 2,4,6-tl-imethylolphenol compound, the said solution being maintained at a pH of less than about 5 for a time suificient to apply E2 References Citeli in the file of this patent UNITED STATES PATENTS to the said material between about 3 and 25 parts by 3357374 f at weight of said resin-forming admixture per 100 parts by 5 32%? .3 g 20, dry weight of cellulose in the cellulose textile material 242-218 a nd thereafter heating the so treated material to remove 2 579'329 M222; g if; the W815! and cure lb: resin-forming ad m to a s 2: 3 :01? ecstantially water-insoluble resin.

9. The method according to clainifi in which the ailno phatic poiyhydric compound is a loweg aliphatic diol.

REFERENCES 

1. A CELLULOSE TEXTILE MATERIAL CONTAINING A SUBSTANTIALLY WATER-INSOLUBLE CONDENSATION RESIN IN AMOUNTS AT LEAST SUFFICIENT TO IMPART IMPROVED CREASE AND WRINKLE RESISTANCE BUT LESS THAN THAT AMOUNT IMPARTING STIFFNESS AND HARSH HAND TO THE SAID TEXTILE MATERIAL, SAID CONDENSATION RESIN BEING THE CURED PRODUCT OF A WATERSOLUBLE RESIN-FORMING ADMIXTURE OF (A) A 2,4,6-TRIMETHYLOLPHENOL COMPOUND SELECTED FROM THE GROUP CONSISTING OF 2,4,6-TRIMETHYLOLEPHENOL, THE ALKALI METAL SALTS OF 2,4,6TRIMETHYLOLPHENOL AND THE ALKALINE EARTH METAL SALTS OF 2,4,6-TRIMETHYLOLPHENOL, AND (B) A WATER-SOLUBLE ALIPHATIC POLYHYDRIC COMPOUND PRESENT IN AMOUNTS OF NO GREATER THAN ABOUT FOUR MOLES PER MOLE OF THE SAID 2,4,6-TRIMETHYLOLPHENOL COMPOUND. 